Tim Drake has always been the sort of Golden Boy of all the Robins. Unlike the others, Tim was groomed to be Robin and not Batman’s eventual replacement. Because of this, Tim is arguably the least tragic of all Robins — at least at the time that he started. Over the years, Tim experienced several big changes in his character.
From Robin to Red Robin to Drake, Tim has undergone a lot in recent years. However, no matter what era of DC continuity or what his codename is, Tim has gone through his fair share of darker moments. At times, he has even made some tough decisions that had some very dire consequences.
Updated by Sage Ashford, December 13th, 2022: As awesome as Tim Drake is, no one's immune to making mistakes. No member of the Bat Family is perfect, and Tim's experienced his fair share of regrets.
15 Named Himself Drake On Earth-3
It's not the worst thing he's done by far, but Tim Drake deciding to don a new costume and go by his last name has certainly got to be one of the most embarrassing. It's a creatively bankrupt decision made by superheroes who can't settle on a name for whatever reason.
All jokes aside, the idea of naming himself Drake seems particularly dangerous due to his close relationship with Bruce Wayne. How long would it take before someone realized the new superhero "Drake" looked suspiciously close to Tim Drake, and from there figured out how Drake connected to Batman?
14 Beat Up Damian In Front Of Crime Alley
Damian and Tim have never been on the best of terms. Part of that has to do with Damian attacking Tim when they first met, but at the time it was more than that. Tim already felt like he'd lost his place in the world after losing his friends and family. When Damian took over as Robin while working with Nightwing, it pushed Tim over the edge.
Things reached a boiling point in Red Robin #14 by Fabian Nicieza, Marcus To, Ray McCarthy, Guy Major, and Sal Cipriano. There, Damian is furious that after all his work, Tim still considers him an enemy he needs backup plans to fight. He strikes out at Tim, leading to Tim handing him a brutal smackdown in the middle of Crime Alley, the place where Bruce lost his parents. It took Dick Grayson appearing to get Tim under control and help him realize his mistake.
13 Tried To Clone Conner After Infinite Crisis
In the aftermath of Infinite Crisis, one of DC's best stories of the 2000s, Tim had seen enough. He'd lost his father, multiple girlfriends, and several of his best friends. With so much taken from him, he wasn't able to let all of it go. It was too much pain to process at once, and rather than continue to try, he decided to try and "fix" the problem.
In Teen Titans, it's revealed that Tim has been trying to clone a new version of Conner. When Cassie finds out, she points out that won't be Conner, but Tim can only think that it'll be "good enough." It was a selfish stance, and fortunately, it didn't work — especially since Conner was brought back to life later.
12 Skipped Stephanie's Funeral
During War Games, DC decided someone needed to pay the price for turning Gotham City into a war zone. Stephanie Brown was chosen to pay that cost, and she passed away at the hands of Black Mask. Though they eventually shut Black Mask down, Tim couldn't even be bothered to look Stephanie's mother in the face at her funeral.
Tim's reasoning was fair enough: he'd already lost so many people he couldn't even emotionally process what had happened. Still, it wasn't exactly the most respectful thing to do. Of course, fans are aware now that Stephanie was still alive and getting ready to join the amazing women that had been Batgirl, but Tim didn't know that at the time.
11 Tried To Kill Batwoman
In some of the best Batman comics post-Rebirth, Tim Drake tried to form the Gotham Knights, an organization that could do more good for Gotham together than any of them could solo. One of their greatest enemies during that era was, interestingly, Tim Drake himself — a Tim Drake from the future who'd seen everything fall apart.
Trapped in the past, Future Tim realized he had a way to fix all of his problems. He just had to kill Batwoman, whose actions would eventually lead to his own dark future. Though all the Gotham Knights got in his way, Tim had trained enough to know all their weaknesses and even shut down Batman. It was mostly luck that led them to save Kate, while Future Tim Drake didn't even regret his actions.
10 Killed & Became the Joker (Batman Beyond)
Though not a story from the comics, the DC Animated Universe turned Tim into the Joker. During the Batman Beyond: Return of the Joker (2000) movie, it was revealed that the Joker once kidnapped him and brainwashed him with chemicals and advanced technology. While Tim was able to fight through what the Joker had done to him, Batman banned him from donning the Robin suit ever again.
In the future, the Joker’s programming begins to take hold once again, turning Tim back into the iconic villain and presenting all-new problems for Neo-Gotham. While this wasn't exactly Tim's fault, it's still one of the darkest turns the character has ever taken. Thankfully, he was stopped by Terry McGinnis' Batman before things became too drastic.
9 Allowed Azrael To Get Out Of Control
During the Knightfall storyline, Bane famously breaks Batman's back, leading Jean Paul Valley to assume the role of Batman. Though Bruce was no longer Batman, Tim still operated as Robin and coached Valley on how to be more like The Dark Knight. However, as Valley began to make more brutal decisions as Batman, Tim stood by and didn't say anything until it was too late.
Valley displayed signs of violence early on in his time as the Dark Knight, and with Tim being such a great detective in his own right, he should have known to alert Bruce early on. Instead, he waited until things were at a crisis point. Even Tim recognized his mistake, pointing it out to Bruce later and apologizing for allowing Valley to go as far as he had.
8 Kept Files on His Teammates
During the JLA: Tower of Babel storyline, readers learned Batman kept files on ways to take down each individual member of the Justice League. Shortly after this, Robin's teammates on the Teen Titans approached him on the issue. Tim then reveals that the story they'd heard was actually true and that he and Batman had files on the Titans as well.
This sent a large rift through the team, as they wondered whether Tim had been corrupted by Batman's inability to trust his teammates. However, Tim was able to work things out with the Titans by talking to them, while Batman was expelled from the League. Still, the team struggled to deal with Tim's mistrust of the group for a long time.
7 Quit Being Robin
After getting into several disagreements with Batman, Tim eventually quit being Robin. He went back to being a normal teenager, hanging out with his friends and focusing on his studies. However, he couldn't let go of his heroic instincts and still helped people he saw in need.
Though it made sense for Tim to want to distance himself from an increasingly paranoid Batman, Tim's actions here were selfish. He took up the job because he believed Batman needed a Robin to balance out his darker impulses, then quit when things got hard. Worse, this opened the door for his ex-girlfriend Stephanie to become Robin, which would lead to her brutal beating at the hands of Black Mask.
6 Created Brother Eye
Brother Eye is a supercomputer and artificial intelligence that was originally created by Batman and Mr. Terrific to help the Justice League better fight crime. However, during Infinite Crisis, Brother Eye decided the only way to save the planet was to wipe out humanity, making it into a major Justice League problem.
As of DC Rebirth, Brother Eye's creator was retconned into being Tim Drake, who created the software that would eventually become Brother Eye. To make matters worse, when an evil version of Tim shows up from the future, he takes advantage of the software and transforms it into Brother Eye as part of his scheme to take out the Bat Family. Though he began with good intentions, Tim accidentally created one of the biggest problems the DC superhero community has ever fought.
5 Refused To Tell Conner About Kissing Wonder Girl
Superboy, Robin, and Wonder Girl were some of the earliest members of Young Justice. The group worked together for years, but during their time with the Teen Titans, Superboy and Wonder Girl became romantically involved. Not long afterward though, Superboy sacrificed himself in battle against Superboy Prime.
In the aftermath of Infinite Crisis, in a weak moment for the both of them, Robin and Wonder Girl shared a kiss. Though Tim technically did nothing wrong, he was also reluctant to tell Conner after he was brought back to life. It's a difficult subject to broach, but Tim still should have been honest about his actions considering Conner was his best friend.
4 Replaced Jason
Tim Drake is the third person in a line of young men who called themselves Robin. After Dick Grayson graduated to become Nightwing, Jason Todd assumed the mantle of Robin in his place. Unfortunately, Jason died in an encounter with the Joker, leading to Tim taking the position a short while later.
While most people didn't have a problem with Tim taking the job, there was one person who did. When Jason Todd came back from the dead, seeing Tim take his place made him feel like his death meant nothing. It made him feel replaceable, which led to him attacking Tim at Titans Tower. Though most people wouldn't think twice about it, Jason certainly saw Tim's actions as unforgivable.
3 Joined The Titans Of Tomorrow
In an alternate future, it's revealed that Tim eventually becomes the successor to Batman. After Batman fell in combat, someone needed to take over the position. The mantle fell to Tim, who had no one else helping him after Dick chose to move on. Surprisingly, Tim became an even darker version of Batman than Bruce ever was.
In this future, Tim began carrying a gun as Batman, going against everything Bruce stood for. Believing a more dangerous time required a more dangerous Batman, he turned Gotham into a police state, brutally eliminating any criminals that got in his way. This version of the Titans was so bad, their past selves saw them and swore they'd never be anything like them.
2 Nearly Killed Johnny Warlock
Of all the mistakes Tim made over the years, one of his greatest has been nearly killing Johnny Warlock. After Warlock almost killed Stephanie Brown, Tim made sure to return the favor. The beating he delivered was so severe, that even Batman became worried about his young sidekick.
Thankfully, Tim didn't take things too far, although there's no telling what he would have done if Batman hadn't shown up. This was a failure at every level for Tim, both almost going against Batman's no-kill rule and forgetting he's supposed to be there to be Batman's light.
1 Nearly Killed Captain Boomerang
During his time as Red Robin, Tim comes close to killing Captain Boomerang. Granted, Boomerang did kill Tim's father, so it makes sense that Tim would come to question Batman's no-kill rule. But Tim did more than question their code — he almost lured Boomerang to his death.
Tim decides to save him in the end, but he went through a lot of work to actually kill Boomerang. Though his actions were understandable, that doesn't make them excusable. This incident was a reminder of just how difficult it is to work alongside someone with such a high standard of crime-fighting as Batman.